Hotels in Shady Side

Q: What hotels do travelers like in Shady Side?

Guests like DoubleTree by Hilton Hotel Annapolis , Graduate by Hilton Annapolis and Historic Inns of Annapolis .

Where to?

Dates

January 2026

February 2026

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Where to stay in Shady Side?

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

CNY726 total

includes taxes & fees

Feb 8 - Feb 9

DoubleTree by Hilton Hotel Annapolis

Annapolis

CNY594 total

includes taxes & fees

Feb 8 - Feb 9

Hilton Garden Inn Annapolis Downtown

Annapolis

CNY717 total

includes taxes & fees

Feb 8 - Feb 9

Crowne Plaza Annapolis by IHG

Annapolis

CNY843 total

includes taxes & fees

Feb 9 - Feb 10

Courtyard by Marriott Annapolis

Annapolis

CNY668 total

includes taxes & fees

Feb 1 - Feb 2

The Westin Annapolis

Annapolis

CNY1,185 total

includes taxes & fees

Jan 13 - Jan 14

Hyatt Place Kent Narrows & Marina

Grasonville

CNY937 total

includes taxes & fees

Jan 19 - Jan 20

Hilton Garden Inn Annapolis

Annapolis

CNY630 total

includes taxes & fees

Feb 1 - Feb 2

Hampton Inn & Suites Annapolis

Annapolis

CNY711 total

includes taxes & fees

Jan 25 - Jan 26

Rod 'N' Reel Resort

Chesapeake Beach

CNY726 total

includes taxes & fees

Jan 18 - Jan 19

Comfort Inn Conference Center

Bowie

CNY773 total

includes taxes & fees

Feb 2 - Feb 3

Sonesta ES Suites Annapolis

Edgewater

CNY732 total

includes taxes & fees

Feb 1 - Feb 2

The Wildset

Downtown St. Michaels

CNY1,604 total

includes taxes & fees

Jan 13 - Jan 14

Graduate by Hilton Annapolis

Annapolis

CNY1,168 total

includes taxes & fees

Jan 21 - Jan 22

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

CNY736 total

includes taxes & fees

Jan 18 - Jan 19

SpringHill Suites by Marriott Annapolis

Annapolis

CNY872 total

includes taxes & fees

Jan 19 - Jan 20

Historic Inns of Annapolis

Historic District

DoubleTree by Hilton Hotel Largo/Washington DC

Upper Marlboro

CNY723 total

includes taxes & fees

Jan 25 - Jan 26

Microtel Inn & Suites by Wyndham Gambrills

Gambrills

CNY617 total

includes taxes & fees

Jan 26 - Jan 27

Best Western Kent Narrows Inn

Grasonville

CNY646 total

includes taxes & fees

Jan 18 - Jan 19

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Budget hotels in Shady Side and vicinity

Best Western Annapolis

Annapolis

CNY544 total

includes taxes & fees

Feb 8 - Feb 9

DoubleTree by Hilton Hotel Annapolis

Annapolis

CNY594 total

includes taxes & fees

Feb 8 - Feb 9

Comfort Inn Largo-Washington DC East

Upper Marlboro

CNY597 total

includes taxes & fees

Jan 22 - Jan 23

Desk, laptop workspace, blackout drapes, iron/ironing board

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

Upper Marlboro

CNY597 total

includes taxes & fees

Jan 18 - Jan 19

Microtel Inn & Suites by Wyndham Gambrills

Gambrills

CNY617 total

includes taxes & fees

Jan 26 - Jan 27

Candlewood Suites Annapolis by IHG

Annapolis

CNY668 total

includes taxes & fees

Jan 16 - Jan 17

Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Grasonville

CNY652 total

includes taxes & fees

Jan 19 - Jan 20

Hilton Garden Inn Annapolis Downtown

Annapolis

CNY717 total

includes taxes & fees

Feb 8 - Feb 9

Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

Upper Marlboro

CNY702 total

includes taxes & fees

Jan 20 - Jan 21

Courtyard Largo Medical Center Drive

Upper Marlboro

CNY718 total

includes taxes & fees

Jan 18 - Jan 19

Hampton Inn & Suites Glenarden/Washington DC

Lanham

CNY723 total

includes taxes & fees

Jan 25 - Jan 26

DoubleTree by Hilton Hotel Largo/Washington DC

Upper Marlboro

CNY723 total

includes taxes & fees

Jan 25 - Jan 26

View all budget hotels

Go beyond your typical stay in Shady Side

Pet friendly

Hot tub

Top landmarks in Shady Side

Shadyside Park

Shadyside Park is 0.4 mi (0.6 km) from central Shady Side, why not stop by during your stay. Our travelers also like this walkable area for its port and restaurants.If you like Shadyside Park, you'll love Maryland Quiet Waters Park and Ellen O. Moyer Nature Park at Back Creek, both just a short drive away.

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Captain Avery Museum

Captain Avery Museum is 0.5 mi (0.8 km) from central Shady Side, why not stop by during your stay. Why not take a stroll along the port and watch the sunset while you're here? If you want to experience more of the culture Shady Side has to offer, head to Shadyside Park, Franklin Point State Park, and Triton Beach.

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Check out reviews of Shady Side hotels guests love

Historic Inns of Annapolis

10/10 Excellent

"H"

Comfort Inn Largo-Washington DC East

10/10 Excellent

"Thomas at check in was great! I arrived before the normal check in time but he went of of his way to make sure I had a room and even found me a bellcart for all my luggage since I had a lot. The room was perfect for my daughter and I and the beds were very comfy!! Loved the indoor pool and free breakfast as well! I’d definitely stay here again!"

WoodSpring Suites Washington DC East Arena Drive

10/10 Excellent

"Parking was easy and secure. They provided us with a parking pass once we checked into our room. The room was clean (for the most part) and the hotel itself was nice. My only issue was that we saw exactly one roach during our stay. This concern me a little because the other wood spring suites I stayed at in PG County had a roach infestation and it made me think this was a franchise thing. However, as far as we know, there was only that one we came across."

Frequently asked questions

How much does a hotel room cost in Shady Side?

You can choose a great hotel in Shady Side from CNY594 with properties to suit all budgets and needs. If you're after an affordable hotel in Shady Side that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Shady Side hotels?

Discover great deals on Shady Side hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. And make sure to check out our last-minute deals on Shady Side hotels.

Can I book Shady Side hotels with free cancellation?

It's easy to book a refundable Shady Side hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Shady Side?

If you're looking for hotels in central Shady Side, check out The Inn at Tacaro Estate. Travelers love The Inn at Tacaro Estate for its location, as well as the seasonal outdoor pool, hot tub and free full breakfast this bed & breakfast offers. Hillsmere and Arundel on the Bay are some of the most central neighborhoods for your Shady Side vacation.

What hotels do travelers like in Shady Side?

Guests like DoubleTree by Hilton Hotel Annapolis, Graduate by Hilton Annapolis and Historic Inns of Annapolis.

Can I book a refundable hotel in Shady Side?

If you need the flexibility to change your plans to Shady Side, most properties provide refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Shady Side if I want a vacation rental instead of a hotel?

If you want to find a good alternative to a hotel, browse our selection of 10 vacation homes.

What will the weather in Shady Side be like during my vacation?

The warmest months in Shady Side are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 40°F. The rainiest months are July and August.

Why should I book my Shady Side accommodation with Hotels.com?

There are plenty of reasons to book your Shady Side travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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